Aniline → Methyl 3-(phenylamino)benzoate

HRID 2422267

反応式

HRID 2422267 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[NH:12]([C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 6115AnilineHCID 10796Cesium carbonateHCID 12070Methyl 3-bromobenzoateHCID 634876Binap, (A+-)-

生成物 1

HCID 614856Methyl 3-(phenylamino)benzoate収率 34.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A mixture of methyl 3-bromobenzoate (5.87 g, 27.3 mmol), aniline (3.73 mL, 41.0 mmol), cesium carbonate (12.5 g, 38.2 mmol), tris(dibenzylidenacetone)dipalladium (0) (1.0 g, 1.09 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.02 g, 1.64 mmol) and toluene (60 mL) was stirred under a nitrogen atmosphere at 80° C. for 16 hrs. The reaction mixture was cooled, washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1) to give the title compound (2.13 g, yield 34%) as pale-yellow crystalsitle compound.

後処理

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1)

出典と根拠

ORDレコード
ord-322484b5bc5e4d83a72afe64281b1bcf
出典データセット
uspto-grants-2011_06
特許番号
US07960369B2

関連ノート

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